Morpholine → HCID 59333542, compound

HRID 1876519Notes

Reaction equation

Cl[C:2]1[N:3]([CH2:24][CH:25]2[CH2:29][CH2:28][O:27][CH2:26]2)[C:4]2[C:9]([N:10]=1)=[C:8]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[N:7]=[C:6]([C:17]1[CH:18]=[N:19][C:20]([NH2:23])=[N:21][CH:22]=1)[N:5]=2.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>CS(C)=O>[N:11]1([C:8]2[N:7]=[C:6]([C:17]3[CH:18]=[N:19][C:20]([NH2:23])=[N:21][CH:22]=3)[N:5]=[C:4]3[C:9]=2[N:10]=[C:2]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[N:3]3[CH2:24][CH:25]2[CH2:29][CH2:28][O:27][CH2:26]2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

Conditions

Temperature: 150 °C

Procedure

Dimethyl sulfoxide (1 ml) was added to a mixture of 5-[8-chloro-6-morpholin-4-yl-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-2-yl]pyrimidin-2-amine (100 mg, 0.24 mmol) and morpholine (63 μl, 0.72 mmol) and the resulting mixture was stirred at 150° C. for 3 hours. The reaction mixture was cooled and then partitioned with chloroform and water, and the organic layer was washed again with water and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by silica gel chromatography (chloroform:methanol=10:0 to 25:1 to 20:1) to give the title compound (75 mg, 67%) as a pale yellow solid.

Workup

temperatureThe reaction mixture was cooled
custompartitioned with chloroform and water
washthe organic layer was washed again with water
dry with materialdried over magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel chromatography (chloroform:methanol=10:0 to 25:1 to 20:1)

Sources & evidence

ORD record: ord-0c804be0a8114b4896e8451a7196ccf0
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309546B2

Reaction notes

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